I've been to Cuba twice, and I didn't find the kind of conditions that Picardo refers to. The roads I travel on were in much better condition than the roads in the DR. There are many crumbling building in Havavna, but overall the intrastructure is much better in Cuba than that in the DR. In addition, the hotels I stayed in were remarkably good, quite reasonably priced, and well-staffed.
The people working in the hotels (I didn't stay in AIs) were experienced and courteous. There were no sankies that I observed, although I heard stories. Most of the staff spoke at least some english, and some spoke several languages fluently. Everyone in Cuba has access to an excellent educational system, and it shows. The people are articulate, literate, and well-informed.
Outside of Havana, in Cienfuegos and Trinadad for example, the streets and the building were spotlessly clean and well-kept. The people were genuinely friendly, and there were very few, or no tigueres around, that I witnessed.
The security was much better in Cuba than in the DR. Of course, you pay for that level of security in other ways, but for a tourist, security is really what matters, not political freedoms.
Based on my experience, which is limited I admit, I can see Cuba being very much a formidable competitor of the DR with regard to tourism. I believ it would be favored over the DR in many respects, and equal to the DR in others.
It is definately a place where visitors feel welcomed, and are encouraged to return. The concept of actually being welcomed is quite the opposite from the overall negative attitude exhibited toward gringos in the DR, not that that attitude it isn't partially justified.